How To Dress Well: 20 Expert Style Tips All Men Should Know

It’s a cliche, but rules, it must be said, are there to be broken. Style is personal and, above all, individual. Some men can pull things off and others can’t. Some men are innately more conservative than others.

So far, so contractual rider. But this all acknowledged, there are nevertheless well-tested guidelines which, if respected, help ensure that any man is dressed as well as possible – regardless of his own unique pizzazz in the wardrobe department.

Think of the pointers below as being the foundation. You bring the bricks and mortar.

Get The Fit Right

There’s little point wearing good clothes if they don’t fit. Few things make a even a great garment look shabby than being too short or too long, too big or too small. So if something doesn’t fit – pay particular attention to across the shoulders and around the chest – don’t buy it. Or, as annoying as it is, don’t wear it anymore.

Of course, some dimensions on some items – suit sleeves and trousers, for example – can be altered. Find a good tailor and do just that.

Opt For Quality Over Quantity

With countless tonnes of clothing ending up in landfill each year, environmental awareness alone should be enough to convince you to buy less. But the incentive is doubled if you’re on any kind of budget or if you appreciate good value.

Higher quality clothes not only tend to look better, they also wear better and therefore last longer. Add in the fact that cheaper garments can suggest all sorts of ethical problems in terms of worker conditions, and saving up might literally save a life.

Care For Your Clothes

Much of what makes your style happens before you even get dressed. There’s the valuable thinking time put into what you’ll wear, of course. But there’s also the tending to the clothes you select. It’s tedious sometimes, but iron your dress shirts, dry clean your suits occasionally, polish your shoes, repair what needs repairing.

It’s not just because your clothes will last longer this way. You’ll look better. Think of all this preparation as being part of the same process as your general grooming.

Classics Endure

Fashion changes – that’s its very reason to exist. If you don’t want to keep chasing trends, or want to rise above it, wear the classics. These are those largely unchanging garments that have formed the bedrock of men’s style for many decades – from button-down shirts to Derby shoes, straight-fit jeans to two-button, single-breasted navy suits.

Classic does not necessarily mean boring – you still style them in your own way. However, it does mean you’ll look dependably good at any time.

Do Sweat The Details

Anyone can put on clothes. It’s the attention you pay to how you put them on that matters.

Some style rules feel overly finicky/uncreative but they do help create an overall good appearance: matching your belt leather to your shoe leather; wearing dress socks with dress shoes; tying a knot that’s right for your collar; not thinking your underwear doesn’t matter because nobody will see it. And so on.

It Pays To Accessorise

Either out of choice or necessity, your clothing can be conservative, even pedestrian, if you accessorise well. It’s in the accessories that you can express your individuality to anyone who’s looking for it – if you’re into watches, invest in a good, versatile one; step up the quality with anything you wear a lot, like belts, shoes or spectacles; introduce flair with highlight touches of colour and pattern on scarves, pocket squares or jewellery.

These tend to be the things people notice. You actual clothes are just backdrop.

Feel At Ease

Feel comfortable in your clothing, psychologically rather than physically (though, wisely, few men will suffer pain for fashion). Unless the occasion absolutely demands it – and sometimes it does – don’t wear anything that you don’t feel right in. It will show.

This doesn’t mean your comfort zone should be limited to T-shirts and sweatpants. You have to push yourself to find a style that’s yours. But make sure it is yours, and not someone else’s.

If In Doubt, Dress Up

Wearing the right clothes for the right setting is both important and respectful but it can be a complicated business. Dress codes are in flux. Some invitations still insist on using contradictory terms the likes of ‘smart casual’. If in doubt, dress up.

It’s the kind of advice your grandmother might give, but she’d be right: nobody ever felt out of place for being too smart. Not being smart enough, however, is painful.

Master Colour, Pattern & Proportion

Menswear has long been a terribly sober business, wrapped up in dated ideas of appropriateness and masculinity. But you don’t have to dress like an undertaker.

Colour, pattern and proportion not only add interest to your clothing, they can help keep you interested in it too. Yes, they are tricky to master. Yes, you need to learn the basics of colour matching and find the shades that complement your complexion. You will make some mistakes. But be bold and experiment occasionally.

Understand Clothing Craft

You can only choose quality clothing if you take the time to examine what you buy – and understand what you’re buying. Look for close, regular stitching; opt (in most cases) for natural fibres; check the standard of finishing; plump for traditional manufacturing techniques like Goodyear-welting; although supply chains are immensely complex, consider the country of origin.

The internet is your friend – do the manufacturer’s claims stand up to scrutiny or are you being sold to?

Embrace Texture

Colour and pattern are both important, but if you really want to elevate an outfit, deploying some considered textures can add yet another dimension. Tactile fabrics like corduroy, silk, suede and fleece can generate a sense of depth or help to create a focal point.

Adding them to your wardrobe will arm you with yet another string to your sartorial bow and allow you to take simple outfits up a gear with ease.

Learn To Layer

Having a good grasp on layering will stand you in good stead when the weather begins to cool and outfit options multiply. Sure, throwing a winter coat on over a T-shirt does the trick, but it’s hardly as interesting as combining a knitted roll neck, a thick flannel shirt and an overcoat, is it?

Experiment with different combinations and use varied textures and colours to create contrast.

Have A Weekday Uniform

Even if your job doesn’t require you to wear specific clothes, having a go-to work outfit can still be useful. Not having to think about what to wear every day will save you time and enable you to perfect your look. It could be as simple as an overshirt worn over an Oxford shirt and jeans.

Buy a few colour variations of each and mix and match to keep things fresh. It’s also easier to add pieces to this set foundation, such as a sweatshirt or overcoat, to cope with changes in weather.

Find What Works For You

Let’s face it, we’re all different. What suits you may not suit someone else and vice versa. Style advice is all well and good up to a point but if you really want to dress well, you need to find what looks good on you and stick to it.

Look at what colours go best with your skin tone, which cut of denim fits your body type best and even take your face shape into consideration when deciding on your next haircut.

Build A Capsule Wardrobe

Having a fully stocked walk-in wardrobe fit for MTV Cribs might be nice but it doesn’t necessarily make it easier to dress well. We often talk about the virtues of a minimalist wardrobe and we firmly believe it’s a sure-fire recipe for sartorial success.

The secret lies in having the basics covered to the highest possible standard, resulting in a highly versatile clothing collection that will have your back across the whole spectrum of social occasions and dress codes.

Don’t Neglect Your Footwear

As Savile Row legend Hardy Amies once said, it’s impossible to be well dressed in cheap shoes. You can be wearing the finest clothes known to man, but if you top it off with subpar footwear it will all have been for nothing.

With that in mind, your shoes should never be an afterthought. Spend a bit of time and money on getting them right and everything else will fall into place.

Experiment With High-Low Dressing

Mixing upscale pieces with everyday essentials is a great way to spice up your style. With this technique, you can dress casual pieces up and smarter pieces down to cover a variety of situations. Try taking a more relaxed approach to tailoring by swapping the shirt out for a tee and the Oxford shoes out for some luxe leather sneakers.

Conversely, you could use the same idea to dress up a workwear staple like an overshirt with smarter pieces like cropped wool trousers, a fine-gauge roll neck and leather Derby shoes. Play around with it and see what works.

Dress For Your Age

People should be able to wear whatever makes them feel good. Still, if you want to look your best, it pays to have a bit of self awareness when it comes to what’s age appropriate.

Skater hoodies, baggy jeans and giant bubble trainers may have been de rigeur when you were a 13-year-old boy. Now that you’re a functioning member of adult society, however, not so much. Stick to the classics and you can’t go wrong.

Invest In Quality Underwear

Dressing well isn’t all about what’s going on on the outside. How can one ever truly be considered properly dressed if what lies beneath isn’t up to scratch? Even if you’re going to be the only one who sees them, investing in nice socks and quality underwear will give your confidence a little boost and put a spring in your step.

Take a look at brands like Sunspel, Zimmerli, Hanro and Derek Rose for some of the best options around.

Find Inspiration On Social Media

Apps like Instagram can be great for sourcing a bit of style inspiration. Search hashtags to find things that interest you and follow accounts that speak to your way of dressing. It can also be good to follow some accounts that aren’t necessarily promoting the type of clothes you’d normally wear.

Sometimes inspiration can be found in unlikely places.